Barbara Windsor And The Kray Twins

Picture this: it’s the swinging Sixties in London, a time of miniskirts, mods, and rockers, and the city’s most notorious gangsters—the Kray twins—are basically running the East End like a couple of terrifying, suited-up kings. Now, add to this mix a pint-sized, peroxide-blonde bundle of energy named Barbara Windsor, best known for her bubbly role in the Carry On films. You might think a tiny comedy actress would have nothing to do with violent criminals, but you’d be hilariously wrong.

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Barbara, who stood at a mighty five feet nothing and had a laugh that could shatter glass, wasn’t just a random fan. She actually socialized with Ronnie and Reggie Kray in their heyday. The twins owned a string of nightclubs, including the infamous Krays’ Esmeralda’s Barn in Knightsbridge, and Barbara was a regular guest.

Can you imagine? One minute she’s filming a scene with Sid James where she loses her dress in a classic farce, and the next she’s sipping champagne next to a man who once smashed a rival’s face into a wall. The contrast is so wild, it’s like finding your grandmother’s knitting needles next to a chainsaw.

A Dinner Date With Danger

According to Barbara’s memoirs, Reggie Kray had a massive crush on her. He was the slightly more charming twin—emphasis on slightly, like a shark that smiles before it bites. One night, Reggie invited her to dinner at a fancy restaurant, and Barbara, being a good sport, agreed.

As she tells it, the evening was going fine until Reggie’s brother Ronnie, the violently unpredictable one (imagine a bull in a china shop, only the bull has a loaded gun), showed up. Ronnie, who was famously paranoid and prone to fits of rage, didn’t take kindly to his brother having a female interest. He glared at Barbara throughout the meal, probably wondering if her bubbly personality was a front for being a police informant.

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But here’s the kicker that most people don’t know: Barbara Windsor once saved the Krays from a potential gangland hit. Or at least, she thought she did. During one late-night party at a club, she overheard some shady guys talking about “sorting out” the twins. Being a loyal, if slightly tipsy, friend, she rushed to warn Ronnie and Reggie.

The twins, ever the gentlemen (in their own twisted way), thanked her profusely and poured her another drink. Later, it turned out the “hit” was just two rival gangsters having a loud argument about a stolen shipment of fur coats. But still—the sheer chutzpah of a five-foot actress acting as a bodyguard for two stone-cold killers is the stuff of legend. It’s like a Chihuahua barking at a pack of wolves and the wolves stepping back going, “Respect, little one.”

The Friendship That Baffled Everyone

Why did the Krays, who had a body count and a reputation for cruelty, adore Barbara so much? Simple: she was funny and genuine. In a world of fake smiles and backstabbing gangsters, Barbara’s laugh was a genuine ray of sunshine—even if that sunshine came with a side of sauciness. Ronnie, who struggled with mental health issues, reportedly loved her for making him laugh, a rare luxury in his dark world.

She’d tease them mercilessly, calling them “boys” and telling them to stop being so mean. And they listened. Once, when Ronnie was sulking about a failed deal, Barbara apparently told him to “cheer up, you look like a constipated bulldog,” and he cracked a smile. Imagine telling a psychopath to smile and living to tell the tale.

The Aftermath: No Tarantino Ending

Eventually, the Krays were arrested in 1968 and sentenced to life in prison. Barbara, by then a huge star, moved on to EastEnders and became a national treasure. But she never forgot her wild nights with the twins. In her later years, she’d joke that Reggie once tried to kiss her, and she had to remind him she was “a good girl”—and that he had lipstick all over his collar from someone else.

Why did she never get hurt? Luck, charm, and the sheer audacity of being Barbara Windsor. She treated them like naughty schoolboys, and they adored her for it. It’s a perfect reminder that sometimes, the most dangerous people in the room can be disarmed by a cheeky smile and a Carry On joke.

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So, next time you’re at a dodgy pub or an awkward party, remember Barbara’s golden rule: confidence beats intimidation. She didn’t cower; she cracked jokes. And while you probably shouldn’t try this at home with actual gangsters, her story is proof that the universe has a weird sense of humor.

Barbara Windsor was a tiny woman who drank with giants—and made them look like fools. The Krays may have ruled the East End, but she had the last laugh, living to tell the tale while their empire crumbled. And honestly, that’s the kind of plot twist even Carry On couldn’t have written.